4-Chlorobiphenyl → (1,1'-Biphenyl)-4-methanol

HRID 642974

Reaction equation

HRID 642974 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[O:14]1CCOC[CH2:15]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O>[C:5]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:7][C:2]([CH2:15][OH:14])=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 163234-ChlorobiphenylHCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Product 1

HCID 19186(1,1'-Biphenyl)-4-methanolYield 80%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-chlorobiphenyl (23 mg, 0.12 mmol), 1,4-dioxane (2 ml) and water (200 μl) were added potassium acetoxymethyl trifluoroborate (44 mg, 0.24 mmol), palladium (II) acetate (14 mg, 0.061 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (50 mg, 0.12 mmol), and potassium phosphate (170 mg, 0.73 mmol) at room temperature. The reaction mixture was heated to reflux overnight under the nitrogen atmosphere. After the reaction mixture was cooled at room temperature, water and ethyl acetate were added to the mixture. After the organic layer was washed with an aqueous saturated sodium chloride solution, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (18 mg, 0.098 mmol, 80%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight under the nitrogen atmosphere
  3. washAfter the organic layer was washed with an aqueous saturated sodium chloride solution
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-0853536012104f8a924b8817fd81f183
Source dataset
uspto-grants-2010_04
Patent number
US07696347B2

Linked notes

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